HCID 131717428, compound → HCID 67906350, compound

HRID 893018Notes

Reaction equation

HRID 893018 reaction equation
S([O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH:18]([C:22]3[N:27]=[C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[N:25]=[C:24]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:23]=3)[CH2:17]2)=[CH:8][C:7]=1[CH3:38])(=O)(=O)C>[OH-].[Na+].CO>[CH3:12][C:11]1[CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][NH:19][CH:18]([C:22]3[N:27]=[C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[N:25]=[C:24]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:23]=3)[CH2:17]2)[CH:8]=[C:7]([CH3:38])[C:6]=1[OH:5]

Participants

4

Reactant 1

HCID 131717428HCID 131717428, compound

Product 1

HCID 67906350HCID 67906350, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2,6-Dimethyl-4-[3-(2,4-bis(1-pyrrolidinyl)-6-pyrimidinyl)piperazinyl)propyl phenol O-mesylate (Part I, 1.0 g) in aqueous sodium hydroxide (25%, 10 ml) and methanol (20 ml) are stirred at 50° under nitrogen for 20 hr. The mixture is cooled and the methanol removed under reduced pressure. The aqueous layer is acidified with aqueous hydrochloric acid (10%) and then the pH adjusted to 8 with aqueous saturated sodium bicarbonate. The product is extracted with methylene chloride (2×). The extracts are washed with water, dried over sodium sulfate and concentrated. The concentrate is crystallized from ether/hexane to give the title compound.

Workup

  1. temperatureThe mixture is cooled
  2. customthe methanol removed under reduced pressure
  3. extractionThe product is extracted with methylene chloride (2×)
  4. washThe extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe concentrate is crystallized from ether/hexane

Sources & evidence

ORD record
ord-f2beaf68b17349aabca6c6b992eb7e1e
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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